Cloud Migration Readiness Assessment

A self-scoring assessment to determine if your business is ready to move to the cloud — and what to address before you do.

How to use this assessment: For each question, circle or check the option that best describes your current situation. Each answer is worth 0, 1, or 2 points. Add up your score at the end of each section and calculate your total. The scoring guide will tell you where you stand and what to do next. Be honest — overestimating readiness leads to failed migrations.

Section 1: Current Infrastructure (6 questions)

Section 2: Applications & Software (6 questions)

Section 3: Security & Compliance (6 questions)

Section 4: Team Readiness (5 questions)

Section 5: Budget & Timeline (5 questions)

#	Question	Not Ready (0)	Partial (1)	Ready (2)
1	Do you have a complete inventory of all servers, workstations, and network devices?	No inventory exists	Partial list, may be outdated	Full, current inventory documented
2	What is the age of your primary server(s)?	7+ years or unknown	4–6 years	Under 4 years or already cloud
3	How reliable is your internet connection?	Frequent outages, under 50 Mbps	Mostly stable, 50–200 Mbps	Reliable, 200+ Mbps, redundant ISP
4	Do you currently use any cloud services (M365, Google Workspace, etc.)?	No cloud services	Email in cloud, files on-prem	Multiple cloud services in use
5	Is your network properly documented (IP scheme, VLANs, firewall rules)?	No documentation	Some docs, may be outdated	Fully documented and current
6	Do you have a current, tested backup of all critical data?	No backups or untested	Backups exist, not recently tested	Regular backups, tested quarterly

#	Question	Not Ready (0)	Partial (1)	Ready (2)
7	Do you have a complete list of all software applications used by your business?	No — we'd have to check each PC	Mostly documented	Full application inventory with licensing
8	Are your line-of-business applications cloud-compatible or SaaS-available?	Legacy apps that require local server	Some cloud-ready, some legacy	All apps are cloud-native or SaaS
9	Do any applications require specific hardware or operating system versions?	Yes, multiple apps with strict requirements	One or two apps with constraints	No hard dependencies
10	How is file storage and sharing currently handled?	Local server shares, no remote access	Mix of local and cloud (OneDrive, etc.)	Cloud-based (SharePoint, Google Drive)
11	Do you have custom or in-house developed applications?	Yes, critical ones with no documentation	Yes, but documented and maintainable	No custom apps, all commercial/SaaS
12	Are your software licenses transferable to cloud/virtual environments?	Unknown or per-device licenses	Some are, some need re-purchasing	All subscription-based or portable

#	Question	Not Ready (0)	Partial (1)	Ready (2)
13	Is multi-factor authentication (MFA) enabled on all cloud accounts?	No MFA anywhere	Some accounts have MFA	MFA on all accounts
14	Do you have a Written Information Security Program (WISP)?	No WISP exists	Have one but it's outdated	Current WISP, reviewed annually
15	Are there industry-specific compliance requirements (HIPAA, PCI, etc.)?	Yes, and we're not sure we're compliant	Yes, mostly addressed	Yes, fully compliant / No specific requirements
16	Do you have endpoint protection (antivirus/EDR) on all devices?	Basic or no antivirus	Antivirus but no central management	Managed EDR on all endpoints
17	Is data classified by sensitivity level?	No classification — all data treated the same	Informal understanding of sensitive data	Formal classification with handling rules
18	Do you have an incident response plan?	No plan exists	Informal process, not documented	Documented plan, team knows roles

#	Question	Not Ready (0)	Partial (1)	Ready (2)
19	How comfortable is your team with cloud-based tools?	Resistant to change, low tech comfort	Mixed — some comfortable, some not	Team regularly uses cloud tools
20	Is there executive/ownership buy-in for cloud migration?	No interest or active resistance	Open to it but not committed	Active support and budget allocated
21	Do you have internal IT staff or an MSP to manage the migration?	No IT support at all	Break/fix IT or part-time support	Dedicated IT staff or managed IT partner
22	Has your team received security awareness training?	Never — no formal training	Once, over a year ago	Annual training with phishing simulations
23	Is there a designated person to champion the migration project?	No — everyone is too busy	Sort of — IT person could lead it	Yes — named project lead with time allocated

#	Question	Not Ready (0)	Partial (1)	Ready (2)
24	Do you understand the monthly cost difference between on-prem and cloud?	No idea what cloud would cost	Rough estimate, not detailed	Detailed TCO comparison completed
25	Is there budget allocated for the migration project?	No budget — hoping it's free	Some budget, may not cover everything	Dedicated migration budget approved
26	What is your migration timeline expectation?	Wants it done in a weekend	Flexible — within 3 months	Realistic — phased over 3–6 months
27	Can your business tolerate some disruption during migration?	Zero tolerance — any downtime is critical	Some planned downtime is acceptable	Flexible — can do after-hours/weekends
28	Have you accounted for ongoing cloud costs (not just migration)?	Only thinking about the move itself	Aware there will be ongoing costs	3-year cost projection completed

📊 Your Total Score

Section 1: _____ + Section 2: _____ + Section 3: _____ + Section 4: _____ + Section 5: _____ = Total: _____ / 56

0 – 18	Not Ready. You need foundational work before considering a cloud migration. Focus on: getting an IT inventory, establishing backups, implementing MFA, and finding a reliable IT partner. Migrating now would create more problems than it solves.
19 – 30	Getting There. You have some pieces in place but significant gaps remain. Address the sections where you scored lowest — especially security and infrastructure. A phased migration (starting with email/files) may work while you shore up the rest.
31 – 42	Almost Ready. Good foundation. You likely have a few specific blockers (legacy apps, compliance questions, or budget constraints). Targeted planning can resolve these. You're a good candidate for a phased migration.
43 – 56	Ready to Migrate. You've done the groundwork. Time to build a migration plan with timelines, stakeholders, and a rollback strategy. Let's go.

📋 Recommendations by Section

Low score in Infrastructure (Section 1)? Start with the basics: document your network, upgrade your internet connection, and implement tested backups. You can't migrate what you don't understand, and you can't rely on cloud services over unreliable internet.

Low score in Applications (Section 2)? This is the most common blocker. Legacy line-of-business apps that only run on a local server need a migration path — either a SaaS replacement, cloud-hosted virtual server, or hybrid approach. Audit your apps first.

Low score in Security (Section 3)? Do NOT migrate to the cloud without addressing security first. Cloud amplifies both benefits and risks. MFA, endpoint protection, and access controls must be in place before you put your data on the internet.

Low score in Team Readiness (Section 4)? Technology is the easy part; people are the hard part. Invest in change management, training, and communication. Identify early adopters who can champion the transition.

Low score in Budget (Section 5)? Cloud migration has upfront costs (migration labor, licensing transitions, training) and ongoing costs (subscriptions, support). Model the 3-year TCO before committing. Cloud is often cheaper long-term, but Year 1 can be expensive.

⚠️ Common Cloud Migration Pitfalls

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